Carbaboranes as Pharmacophores: Properties, Synthesis, and Application Strategies

Synthesis of 10‐Methylsulfide and 10‐Alkylmethylsulfonium nido‐Carborane Derivatives: B–H···π Interactions between the B–H–B Hydrogen Atom and Alkyne Group in 10‐RC≡CCH2S(Me)‐7,8‐C2B9H11

“…In all of the structures, one of the substituents at the sulfur atoms (Me in 7 and 10, and CH 2 C≡CH in 8) is turned in the direction of the B(9)-B(10) boron edge bearing the bridging hydrogen in such a way that the B(9)-B(10) and S-C bonds lay nearly in the same plane (see Table 1), and two CH hydrogen atoms are directed towards the B(9)H and B(5)H hydrogen atoms (the CH···HB distances are 2.473-2.774 Å). (8) with the atom numbering scheme (displacement ellipsoids are drawn at the 50 % probability level) -front view (left) and top view (right).…”

“…1 (20 mL) was heated under reflux for 24 h. Then the reaction mixture was cooled to room temp., and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica using CHCl 3 as the eluent to give 0.22 g (72 %) of white crystalline solid 10-HC≡CCH 2 (Me)S-7,8-C 2 B 9 H 11 (8 (20 mL) was heated under reflux for 24 h. Then the reaction mixture was cooled to room temp., and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica using CHCl 3 as the eluent to give 0.28 g (73 %) of white oily solid 10-C 6 H 5 C≡CCH 2 (Me)S-7,8-C 2 B 9 H 11 (9 (20 mL) was heated under reflux for 24 h. Then the reaction mixture was cooled to room temp., and the solvent was removed under reduced pressure.…”

“…[1] Currently, carborane chemistry is growing at an accelerating pace and generates more than 300 new publications each year, with many of them reporting new advances in medicine, nanomaterials, and other applications. [2,3] The past decade demonstrates a growing interest in various aspects of medicinal chemistry of carboranes [4,5] including their use as pharmacophores in drug design, [6][7][8] HIV protease inhibitors, [9] radionuclide imaging, [10] and boron neutron capture therapy (BNCT) of cancer. [11][12][13] The general approach to the synthesis of carborane-based compounds for BNCT and radionuclide diagnostics lies in derivatization at one of the CH vertices of the carborane cage.…”

Facile Docking and Scoring Studies of Carborane Ligands with Estrogen Receptor

“…1,2 In terms of size and lipophilicity, carboranes occupy the 3-D space generated by a hypothetically rotating benzene ring and are more lipophilic than the benzene ring.…”

Dicarba-closo-dodecarborane-containing half-sandwich complexes of ruthenium, osmium, rhodium and iridium: biological relevance and synthetic strategies

“…Another potential interest in the combination of dicarba-closododecarboranes and half-sandwich complexes of ruthenium, 110 osmium, rhodium and iridium for biological applications lies in the spherical geometry, the steric hindrance and the very strong hydrophobic character of dicarba-closododecarboranes: 36 Indeed, a dicarba-closo-dodecarborane molecule has a diameter of about 1 nm and a volume approximately 40% larger than the volume of a rotating phenyl group. 14 The degree of potential functionalization of dicarba-closo-dodecarboranes being much higher than that of 5 phenyl rings, dicarba-closo-dodecarboranes are considered as convincing bioisosteres for aryl, cycloalkyl or adamantyl units. For instance, this approach has been used by Valliant and co-workers to synthesise an analogue compound of tamoxifen in-which the A phenyl group has been substituted 10 by an o-dicarba-closo-dodecarborane unit.…”